09/28/2026
🍂 Where to go this weekend in Chicago & the suburbs? Save this — I rounded up the best events for October 2–4!
Pumpkins, Oktoberfest, apple fest, live music, and plenty for the kids. Pick your weekend plan 👇
1. 🎃 The Great Highwood Pumpkin Festival | Highwood
📅 Oct 1–4 · Fri 4–10 PM, Sat 12–10 PM, Sun 12–9 PM
📍 Downtown Highwood & Everts Park, 111 North Ave, Highwood, IL 60035
One of the biggest pumpkin festivals in the suburbs. Expect walls of carved pumpkins, carnival rides, two live music stages, kids' and pet costume contests, and a pie-eating contest. The pumpkin walls light up Saturday at 7 PM, and you won't want to miss it.
💵 Free entry (carve a pumpkin for the wall: $2 donation)
👨👩👧 Families / kids / adults
🔗 celebratehighwood.org/pumpkin-fest
2. 🎸 Harmony Fest featuring the Taste of Arlington Heights | Arlington Heights
📅 Fri Oct 2, 5–11 PM · Sat Oct 3, 3–11 PM
📍 Harmony Park, 7 S Vail Ave, Arlington Heights, IL 60005
Free concerts downtown plus food from about 20 local restaurants. Saturday's lineup is Fearless (a Taylor Swift tribute), Y2K, and Mike & Joe. There's also a Kids' Zone.
💵 Free
👨👩👧 Families / adults
🔗 vah.com/explore/harmony_fest_featuring_the_taste_of_arlington_heights.php
3. 🍺 Oktoberfest at Naper Settlement | Naperville
📅 Fri Oct 2, 5–10 PM · Sat Oct 3, 3–10 PM
📍 Naper Settlement, 523 S Webster St, Naperville, IL 60540
A real Oktoberfest at an outdoor history museum. You'll find German food, one of the area's biggest b**r selections, and oompah music. Saturday adds a stein-holding contest and inflatables for the kids.
💵 Adults $25 · Kids 4–12 $15 · Under 4 free
👨👩👧 Adults / families
🔗 napersettlement.org/237/Oktoberfest
4. 🍎 Lincoln Square Ravenswood Apple Fest | Chicago
📅 Fri Oct 2, 3–7 PM · Sat–Sun Oct 3–4, 9 AM–6 PM
📍 N. Lincoln Ave between W. Lawrence & W. Sunnyside, Chicago
The 39th year of this fall favorite. Shop fresh apples and c***r from Midwest farms and browse 100+ vendors, with live music and kids' activities all weekend.
💵 $5 suggested donation
👨👩👧 Families / adults
🔗 lincolnsquare.org/apple-fest
5. 🍏 C***r & Ale Festival at The Morton Arboretum | Lisle
📅 Sat Oct 3, 12–3 PM
📍 The Morton Arboretum, 4100 Illinois Route 53, Lisle, IL 60532
Taste hard c***r and seasonal b**r from 30+ breweries and c***ries surrounded by fall color. Tickets include 20 tastings.
💵 $75 (members $65) · VIP $85 · Designated driver $35 · Kids 4–17 $12
👫 Adults 21+ (kids' tickets available)
🔗 mortonarb.org/explore/activities/events/c***r-ale-festival
6. 🥨 Octoberfest | Schaumburg
📅 Sat Oct 3, 12–5 PM
📍 Meineke Park, 220 E. Weathersfield Way, Schaumburg, IL
A family festival from the Park District with live music, food trucks, face painting, inflatables, and character visits.
💵 Free entry · $10 activity wristband
👨👩👧 Families / kids
🔗 parkfun.com/event/octoberfest
7. 🌾 Autumn Harvest Fest | Schaumburg
📅 Sun Oct 4, 12–4 PM
📍 Heritage Farm at Spring Valley, 201 S. Plum Grove Rd, Schaumburg, IL
Step back into 1880s farm life. Kids can decorate pumpkins and do crafts and games, and a wagon shuttle brings you to the farm.
💵 $5/person or $20/family · 2 and under free
👨👩👧 Families / kids
🔗 parkfun.com/event/autumn-harvest-festival
8. 🎃 Northbrook Autumnfest | Northbrook
📅 Sat Oct 3, 1–4 PM
📍 Meadowhill Park, 1479 Maple Ave, Northbrook, IL 60062
Pumpkin chucking, a petting zoo, horse trolley rides, bounce houses, and a free pumpkin for every kid.
💵 Free
👨👩👧 Families / kids
🔗 nbparks.org/event/autumnfest
9. 🍩 Family Fall Fest | Elmhurst
📅 Sat Oct 3, 9 AM–12 PM
📍 The Depot at Wild Meadows Trace, 511 S York St, Elmhurst
Trick-or-treating, a corn maze inflatable, carnival games, and six food trucks. Come in costume!
💵 Free
👨👩👧 Families / kids
🔗 epd.org/news/family-fall-fest
10. 🦁 Fall Fest at Lincoln Park Zoo | Chicago
📅 Oct 2–4 (the festival runs through Nov 1) · Zoo open 8 AM–5 PM
📍 Lincoln Park Zoo, 2001 N. Clark St, Chicago, IL 60614
A pumpkin patch, s'mores, photo ops, and animal enrichment at 3 PM daily. Live pumpkin carving on Saturday and Sunday.
💵 Free entry · some rides cost extra · parking $35–45
👨👩👧 Families / kids
🔗 lpzoo.org/event/fall-fest
11. 🎨 West Town Art Walk | Chicago
📅 Oct 2–4 · Galleries: Fri 5–8 PM, Sat 10 AM–6 PM, Sun 11 AM–6 PM
📍 West Town: Chicago Ave, Hubbard St, Grand Ave
40+ galleries, shops, and restaurants showing work by local Chicago artists. Free public art tours run at 1 PM Saturday and Sunday, plus free pedicab rides.
💵 Free
👫 Adults / couples
🔗 westtownchamber.org/west-town-art-walk
12. 🛍️ Maxwell Street Market | Chicago
📅 Sun Oct 4, 10 AM–3 PM
📍 Maxwell St between Halsted St & Union Ave, Chicago
Chicago's oldest market, and this is the last one of the 2026 season. Come for street food, vintage finds, handmade goods, and live music.
💵 Free
👨👩👧 Everyone
🔗 choosechicago.com/articles/shopping-and-fashion/maxwell-street-market
13. 🎡 Mokena Family Fall Fest | Mokena (for the south suburbs)
📅 Oct 1–4 · Carnival: Fri 5:30–10 PM, Sat 1–10 PM, Sun 1–5 PM
📍 Yunker Park & The Oaks, 10824 La Porte Rd, Mokena
A carnival with rides, live concerts Friday and Saturday, a b**r tent, and kids' activities.
💵 Parking $5 (cash) · unlimited rides $30–35/day
👨👩👧 Families / kids
🔗 mokenapark.com/mokenafamilyfallfest
Save this so you don't lose it 📌 and send it to the friends you want to spend this weekend with!
